A standard achiral electrophilic fluorinating reagent is sold under the registered trade mark Selectfluor. This reagent described in U.S. Pat. No. 5,086,178 is as follows:
The most efficient chiral reagent for electrophilic fluorination is a mixture of Selectfluor and a cinchona alkaloid as a chiral transfer reagent; see Shibata N et al., J. Am. Chem. Soc. 2000, 122, 10728-10729 and Shibata N et al., J. Am. Chem. Soc. 2001, 123, 7001-7009. This reaction involves generation of an intermediate fluorinated cinchona alkaloid. The intermediate fluorinated cinchona alkaloid described by Shibata (see above) has been found to be less reactive than desirable and to achieve varying levels of enantiomeric excess and/or yield, depending on the substrate.
The following compound, 1,4-diazabicyclo[2.2.2]octane, is known in the art by the acronym DABCO:
